Synthesis and SAR studies of pyrazole-3-carboxamides and -3-carbonyl thioureides including chiral moiety: Novel candidates as antibacterial agents

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Published: Aug 14, 2018
DOI: https://doi.org/10.2298/JSC170313029B
Keywords:
biological activity chiral amino alcohols pyrazole heterocyclic compounds

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Ishak Bildirici
Van Yuzuncu Yil University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Van
Adnan Cetin
Muş Alparslan University, Faculty of Education, Department of Science, 49250, Mu
Nurettin Menges
Van Yuzuncu Yil University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Van
Yusuf Alan
Muş Alparslan University, Faculty of Science and Arts, Department of Biology, 49250, Muş

Abstract

A series of tetrasubstituted pyrazole-3-carboxamides (3a–c) and pyr­azole-3-carbonyl thioureides (6a–c) were synthesized and their structures char­ac­terized by IR, NMR and elemental analysis. The antibacterial potential against specific Gram-positive and Gram-negative strains and the antifungal activities of all novel compounds were investigated. Structure–activity relation­ships (SAR) studies and some theoretical parameters (ClogP, CMR, PSA and ESP) of the compounds were performed on these two pyrazole derivatives. Pyrazole-3-carboxylate ester 2 was used for the synthesis of the carboxamide derivatives. The reactions of pyrazole-3-carbonyl isothiocyanate 5 with appro­priate chiral amino alco­hols were utilized for synthesizing the thioureide deri­vatives. Both of these types of pyrazole derivatives including a chiral moiety exhibited pronounced antibacterial activities. According to the present in vitro study, some of the pro­mising compounds might be new candidates for a new generation of antibacterial drugs.

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How to Cite
[1]
I. Bildirici, A. Cetin, N. Menges, and Y. Alan, “Synthesis and SAR studies of pyrazole-3-carboxamides and -3-carbonyl thioureides including chiral moiety: Novel candidates as antibacterial agents”, J. Serb. Chem. Soc., vol. 83, no. 7-8, pp. 795–807, Aug. 2018.
Issue
Vol. 83 No. 7-8 (2018)
Section
Organic Chemistry

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References

J. He, S. Li, Y. Deng, H. Fu, B. N. Laforteza, J. E. Spangler, J. Q. Yu, Science 343 (2014) 1216

A. E. Rashad, A. H. Shamroukh, M. I. Hegab, H. M. Awad, Acta Chim. Slov. 52 (2005) 429

X. H. Liu, B. F. Ruan, J. Li, F. H. Chen, B. A. Song, H. L. Zhu, J. Zhao, Mini Rev. Med. Chem. 11 (2011) 771

B. S. Sekhon, J. Pest. Sci. 34 (2009) 1

R. A. Sheldon, Chirotechnology: industrial synthesis of optically active compounds, CRC press, 1993, p. 61

S. D. Roughley, A. M. Jordan, J. Med. Chem. 54 (2011) 3451

S. Saeed, N. Rashid, P. G. Jones, M. Ali, Eur. J. Med. Chem. 45 (2010), 1323

J. J. Liu, M. Y. Zhao, X. Zhang, X. Zhao, H. L. Zhu, Mini Rev. Med. Chem. 13 (2013) 1957

V. Alagarsamy, V. R. Solomon, G. Krishnamoorthy, M. T Sulthana, B.Narendar, J Serb. Chem. Soc. 12 (2015) 1471

J. Jr. Schulman, R. P. Keating, J. Biol. Chem. 183 (1950) 215

M. N. Umar, M. Shoaib, M. Sadiq, M. Ayaz, S. Miskeen, I. Shah, S. W. Khan, Pharm Chem J. 6 (2016) 382

C. Bolognesi, N. Holland, Mutation Research, 770 (2016) 183

B. Wang, Y. Ma, L. Xiong, Z. Li, Chin. J. Chem. 30 (2012) 815

P. A. Yonova, G. M. Stoilkova, J. Plant Growth Regul. 23 (2005) 280

B. S. Gerstenberger, M. R. Rauckhorst, J. T. Starr, Bulg. J. Plant Physiol. 23 (1997) 72

L. Jiang, H. T. Zheng, T. Y. Liu, L. Yue, Y. C. Chen, Tetrahedron, 63 (2007) 5123

T. K. Venkatachalam, A. O. Vassilev, A. Benyunov, O. O. Grigoriants, Lett. Drug Des. Discov. 4 (2007) 318

S. N. Manjula, N. Malleshappa Noolvi, K. Vipan Parihar, Eur. J. Med. Chem. 44 (2009) 2923

S. Madabhushi, K. K. R. Mallu, V. S. Vangipuram, S. Y. Kurva, C. Poornachandra, G. Kumar, Bioorg. Med. Chem. Lett. 24 (2014) 4822

E. Sievänen, Molecules, 12 (2007) 1859

J. Liu, S. Yang, X. Li, H. Fan, P. Bhadury, W. Xu, J. Wu, Z. Wang, Molecules, 15 (2010) 5112

S. A. Santamaria, V. G. Fernandez, V. Gotor, Eur. J. Org. Chem. 15 (2009) 2533

K. Rangappa, C. Karam, R. Thippeswamy, M. N. Bhari, Arch. Pharm. Chem. Life Sci. 348 (2015) 299

R. Katoch-Rouse, O. A. Pavlova, T. Caulder, A. F. Hoffman, A. G. Mukhin, A. G. Horti, J. Med. Chem. 46 (2003) 642

K. L. Kees, J. J. Fitzgerald, K. E. Steiner, J. F. Mattes, B. Mihan, T. Tosi, D. Mondoro, M. L McCaleb, J. Med. Chem. 39 (1996) 3920

B. E. Fink, D. S. Mortensen, S. R. Stauffer, Z. D. Aron, J. A. Katzenellenbogen, Chem. Biol. 6 (1999) 205

A. A. Bekhit, A. Hymete, E. D. A. Bekhit, A. Damtew, Y. H. Aboul-Enein, Mini Rev. Med. Chem. 10 (2010) 1014

L. C. Behr, R. Fusco, C. H. Jarboe, Ed. A. Weissberger, Interscience Publishers, New York, 1967, p. 122

R. H. Wiley, L. C. Behr, R. C. Fusco, H. Jarboe, Interscience Publishers: John Wiley Sons, 1967, p 3

A. Idhayadhulla, R. Surendra Kumar, A. Nasser. Acta Chim. Slov., 59 (2012) 405

D. M. Bailey, P. E. Hansen, A. G. Hlavac, E. R. Baizman, J. Pear, A. F. DeFelice, M. E. Feigensonf, J. Med. Chem. 28 (1985), 256

T. L. Siddall, D. G. Ouse, Z. L. Benko, G. M. Garvin, J. L. Jackson, J. M. McQuiston, M. J. Ricks, T. D. Thibault, J. A. Turner, J. C. VanHeertum, M. R. Weimer, Pest. Manag. Sci. 58 (2002) 1175

M. Londershausen, Pestic. Science 48 (1996) 269

C. Chen, K. Wilcoxen, J. R. McCarthy, Tetrahedron Lett. 39 (1998) 8229

S. R. Stauffer, C. J. Coletta, R. Tedesco, G. Carlson, K. Nishiguchi, J. Sun, B. S. Katzenellenbogen, J. A. Katzenellenbogen, J. Med. Chem. 43 (2000) 4934

H. Park, K. Lee, S. J. Park, B. Ahn, J. C. Lee, H. Y. Cho, K. I. Lee, Bioorg. Med. Chem. Lett. 15 (2005) 3307

M. Kamel, Acta Chim. Slov. 62 (2015) 136

T .D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, L. F. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. D. Anderson, E. G.Burton, J. N. Cogburn, S. A. Gregory, C. M. Koboldt, W. E. Perkins, K. A. Seibert, W. Veenhuizen, Y. Y. Zhang, P. C. Isakson, J. Med. Chem. 40 (1997) 1347

T. L. Gilchrist, Heterocyclic Chemistry, Longman, University of Liverpool, New York, 1997, p. 210

M. A. P. Martins, C. M. P. Pereira, P. P. Beck, M. Machado, V. M. Teixeira, H. G. Zanatta, N. Bonacorso, Tetrahedron Lett. 44 (2003) 6669

J. A. Joule, K. Mills, Heterocyclic Chemistry at a Glance, Blackwell Publishing, Oxford, 2007, p. 183

N. K. Terrett, A.S. Bell, D. Brown, P. Ellis, Bioorg. Med. Chem. Lett. 6 (1996) 1819

J. Alemán, S. Cabrera, Chem.Soc. Reviews, 42 (2013) 774

A. Cetin, İ. Bildirici, J. Saudi Chem Soc. (2016), doi.org/10.1016/j.jscs.2016.05.008

A. P. David, J. P. Mc Cuen, Manual of BBL Product sand Laboratory Procedures, Sixth Edition, U.S.A, 1988, p. 70

L. J. Bradshaw, Laboratory Microbiology, 4th Ed. Printed in U.S.A. 1992, p. 435

S. Ren, R. Wang, K. Komatsu, P. Bonaz-Krause, Y. Zyrianov, C. E. McKenna, C. Csipke, Z. A. Tokes, E. J. Lien, J. Med. Chem. 45 (2002) 410.